Diethyl Ether → HCID 20346838, compound

HRID 1701509Notes

Reaction equation

HRID 1701509 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH3:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[N:13]1[CH2:18][N:17]([CH2:19][CH2:20][OH:21])[CH2:16][N:15]([CH3:22])[C:14]1=[S:23].C(OCC)C>C1(C)C=CC=CC=1>[C:1]([O:21][CH2:20][CH2:19][N:17]1[CH2:18][N:13]([C:7]2[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=2[CH3:5])[C:14](=[S:23])[N:15]([CH3:22])[CH2:16]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6367Acetyl chlorideHCID 20346840HCID 20346840, compound

Product 1

HCID 20346838HCID 20346838, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetyl chloride (0.168 g, 1.5 mmole) was added dropwise with stirring to a cooled solution of 1-(2,4-dimethylphenyl)-5-(2-hydroxyethyl)-3-methyl-tetrahydro-s-triazin-2[1H]-thione (0.60 g, 1 mmole) in dry toluene (30 ml). After 10 minutes the solution was allowed to warm to room temperature and stirring was continued for a further 3 hours. The solution was filtered and the solvent removed under vacuum. The product was chromatographed on a column of silica eluting with dichloromethane containing 2% methanol to yield an oil. Trituration with diethyl ether gave 5-(2-acetoxyethyl)-1-(2,4-dimethylphenyl)-3-methyl-tetrahydro-s-triazin-2[1H]-thione (0.24 g, 35%), m.p. 80°-83° C.

Workup

  1. waitwas continued for a further 3 hours
  2. filtrationThe solution was filtered
  3. customthe solvent removed under vacuum
  4. customThe product was chromatographed on a column of silica eluting with dichloromethane containing 2% methanol
  5. customto yield an oil

Sources & evidence

ORD record
ord-f9c977698eaf47fdb835e9c7adc7b2b9
Source dataset
uspto-grants-1980_03
Patent number
US04193994

Reaction notes

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